This invention relates to novel pyridine sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. Nos. 4,579,583 and 4,690,707 disclose herbicidal pyridinesulfonylureas of the formula ##STR1## wherein XA is NR.sub.6 R.sub.7; and
R.sub.6 and R.sub.7 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkoxyalkyl, C.sub.1 -C.sub.4 cyanoalkyl, or taken together form a 5- or 6-membered heterocyclic ring which may also contain O, S, SO or NR.sub.8. PA0 R.sub.2 is H, Cl, Br or CH.sub.3. PA0 R.sub.1 is NH(C.sub.1 C.sub.4)alkyl or N(C.sub.1 -C.sub.4 alkyl).sub.2. PA0 R.sub.1 is NH.sub.2, NH(C.sub.1 -C.sub.4)alkyl or N(C.sub.1 -C.sub.4 alkyl).sub.2. PA0 R is H or CH.sub.3 ; PA0 R.sub.1 is H, F, Cl, Br, I, CN, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, OCF.sub.2 H, SCH.sub.3, SCF.sub.2 H, C.sub.1 -C.sub.3 alkylsulfonyl or SO.sub.2 CF.sub.2 H; PA0 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 haloalkyl, CN, OH, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3)2, C.sub.1 C.sub.2 alkyl substituted by CN, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or C(O)R.sub.5 ; PA0 R.sub.3 is H, C.sub.1 C.sub.4 alkyl or C.sub.1 -C.sub.2 haloalkyl; or PA0 R.sub.2 and R.sub.3 may be taken together as --(CH.sub.2).sub.n --or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- or ##STR6## R.sub. is H, F, Cl or CH.sub.3 ; R.sub.5 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA0 R.sub.6 is H, C.sub.1 -C.sub.2 alkyl or phenyl; PA0 R.sub.7 is H or CH.sub.3 ; PA0 n is 2, 3, 4 or 5; PA0 p is 0 or 1; PA0 A is ##STR7## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalky 1, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA0 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl) amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR8## m is 2 or 3; Q.sub.1 and Q.sub.2 are independently O or S; PA0 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA0 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA0 Y.sub.1 is O or CH.sub.2 ; PA0 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA0 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA0 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA0 Y.sub.3 is H or CH.sub.3 ; PA0 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA0 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA0 R.sub.2 is C.sub.1 -C.sub.2 haloalkyl, OH, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 cycloalkyl or C(O)R.sub.5 ; PA0 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.2 haloalkyl; or R.sub.2 and R.sub.3 are taken together as --(CH.sub.2).sub.n -- or ##STR10## and n is 2 or 3. PA0 W is O; PA0 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; PA0 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sub.a, ##STR11## OCF.sub.2 H, SCF.sub.2 H, OCF.sub.2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3; and PA0 Z is CH or N. PA0 R.sub.2 is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, CF.sub.2 H, OH, OCH.sub.3, CH.sub.2 SCH.sub.3, cyclopropyl or C(O)R.sub.5 ; PA0 R.sub.3 is H, CH.sub.3 or CH.sub.2 CH.sub.3; or PA0 R.sub.2 and R.sub.3 are taken together as --(CH.sub.2).sub.n -- or ##STR12## R.sub.5 is H, CH.sub.3, OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; and PA0 R.sub.6 is H or C.sub.1 -C.sub.2 alkyl. PA0 A is A-1; PA0 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3; and PA0 Y is CH.sub.3, OCH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA0 R is H; PA0 R.sub.1 is H; and PA0 P is O. PA0 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, CN, C.sub.1 -C.sub.2 alkyl substituted by CN or C.sub.1 -C.sub.2 alkoxy, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA0 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.2 haloalkyl; or PA0 R.sub.2 and R.sub.3 are taken together as --(CH.sub.2).sub.n -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; and PA0 n is 4 or 5. PA0 W is O; PA0 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; PA0 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sub.a, ##STR13## OCF.sub.2 F, SCF.sub.2 H, OCF.sub.2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3; and PA0 Z is CH or N. PA0 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, CN, CH.sub.2 CN, CH.sub.2 OCH.sub.3, alkyl or propargyl; and PA0 R.sub.3 is H, CH.sub.3 or CH.sub.2 CH.sub.3. PA0 A is A-1; PA0 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3; and PA0 Y is CH.sub.3, OCH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA0 R is H; PA0 R.sub.1 is H; and PA0 p is O. PA0 R.sub.2 is C.sub.1 -C.sub.2 haloalkyl, OH, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 cycloalkyl or C(O)R.sub.5 ; PA0 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.2 haloalkyl; or PA0 R.sub.2 and R.sub.3 are taken together as --(CH.sub.2).sub.n --, or ##STR14## and n is 2 or 3. PA0 W is O; PA0 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; PA0 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sub.a, ##STR15## OCF.sub.2 H, SCF.sub.2 H, OCF.sub.2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3; and PA0 Z is CH or N. PA0 R.sub.2 is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, CF.sub.2 H, OH, OCH.sub.3, CH.sub.2 SCH.sub.3, cyclopropyl or C(O)R.sub.5 ; PA0 R.sub.3 is H, CH.sub.3 or CH.sub.2 CH.sub.3; or PA0 R.sub.2 and R.sub.3 are taken together as --(CH.sub.2).sub.n --, or ##STR16## R.sub.5 is H, CH.sub.3, OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA0 and PA0 R.sub.6 is H or C.sub.1 -C.sub.2 alkyl. PA0 A is A-1; PA0 X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3; and PA0 Y is CH.sub.3, OCH.sub.3, CH.sub.2 CH.sub.3, CH.sub.20 CH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA0 R is H; PA0 R.sub.1 is H; and PA0 p is O. PA0 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, CN, C.sub.1 -C.sub.2 alkyl substituted by CN or C.sub.1 -C.sub.2 alkoxy, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA0 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.2 haloalkyl; or PA0 R.sub.2 and R.sub.3 are taken together as --(CH.sub.2).sub.n -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; and PA0 n is 4 or 5. PA0 W is O; PA0 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; PA0 Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sub.a, ##STR17## OCF.sub.2 F, SCF.sub.2 F, OCF.sub.2 Br, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3; and PA0 Z is CH or N. PA0 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, CN, CH.sub.2 CN, CH.sub.2 OCH.sub.3, allyl or propargyl; and PA0 R.sub.3 is H, CH.sub.3 or CH.sub.2 CH.sub.3. PA0 A is A-1; PA0 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3; and PA0 Y is CH.sub.3, OCH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA0 R is H; PA0 R.sub.1 is H; and PA0 p is O. PA0 X.sub.5 is Cl, NH.sub.2 or NHC(CH.sub.3).sub.3; PA0 R.sub.1 is H, R.sub.3 is H, R.sub.4 is H, p is O and X.sub.5 is NH.sub.2, then PA0 R.sub.2 is other than H. PA0 L is a leaving group such as Cl, Br, I, alkyl sulfide, etc.;
U.S. Pat. No. 4,544,401 discloses herbicidal pyridine sulfonylureas of the formula ##STR2## wherein R.sub.1 is NR.sub.6 R.sub.7; and
EP-A-101,670 discloses a process for the preparation of herbicidal sulfonylureas of the formula ##STR3## wherein A is --C.dbd.N--; and
U.S. Pat. No. 4,518,776 discloses a process for the preparation of herbicidal sulfonylureas of the formula ##STR4## wherein A is --C.dbd.N--; and